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Entries in Best Magazine Covers of the 2000s (1)


16 Best Magazine Covers of the 2000s Featuring Funny People


The 2000s had its ups and downs. In started out pretty lousy, then it got better, and then got crummy again.  A humorless void filled much of the first half and it wasn't until the latter part of the 00's that a roaring new golden age of comedy was under way and print began seeking out funny people for their mags.  They say in the world of business, when a CEO hits the front cover of Forbes, it's time to short the stock.  Fortunately, it doesn't always hold true in the world of comedy.  Here are the best magazine covers of the decade based on the cover's creative direction and its moment in the zeitgeist.

16) Rolling Stone - Tom Green - April 2001 | It's Not Easy Being Tom Green

He's been keeping busy ever since, but the Tom Green era peaked with a notorious trifecta of testicular cancer, a cult hit/box office bomb, and a marriage to Drew Barrymore.

 15) Newsweek - Stephen Colbert - June 2009 | Why I Took This Crummy Job

Stephen Colbert attempted to shake the nation out of its war apathy with one of his biggest stunts yet:  a Baghdad blowdry.  His broadcasts from Iraq were the stuff that shiny television awards were made for.

14) GQ - Jimmy Kimmel - November 2008 | Inaugurate This!

Kimmel gets the double cover treatment in GQ's recasting of the 2008 election as a choice between JFK and Nixon.

13) Shape - Jenna Fischer - November 2009 | Jenna Fischer: Smart, Funny, and Fit

Benign Shape magazine puts out a Maxim-worthy cover when readers get a good look at Fischer on a Casual Friday.

12) Ghettoblaster - Eugene Mirman - Spring 2009

11) GQ - Bruno- July 2009 | A Man Among Men: Bruno

10) Bust - Amy Sedaris - June/July 2008 | For a Good Time, Call Amy Sedaris

9) Rolling Stone - Jackass - February 2001 | 'Jackass' Mimic Injured

8) Mad - Family Guy - October 2005 | MAD #458 Preview (PDF)

Mad incisively zings Family Guy but the series turned out to be a juggernaut.  Four years later, a broke and desperate Marge Simpson would find herself pushing her wares in the Playboy Grotto. There's only one way to go when you're on top.

7) Time Out New York - Flight of the Conchords - January 2009 | The Kiwi Comics are #1 in Brooklyn

108 fitness tips to keep your New Year's resolutions on track--just in time for Season 2 of Flight of the Conchords.

6) Esquire - Dave Chappelle - May 2006 | Heaven Hell Dave Chappelle

5) Entertainment Weekly - Conan O'Brien - January 2008 | Conan O'Brien's Strike Diary Revealed!

Remember the WGA strike and all those gruff, bearded late night hosts? Remember the panic and the jolt of fear that ripped through us when LOST was delayed and none of our shows were on and we all presumed we'd be living off cans of beans and YouTube forever? 

4) Vanity Fair - Female Comedians - April 2008 | Who Says Women Aren't Funny?

Vanity Fair eats its words after Vanity Fair said that women aren't funny.

3) Rolling Stone - Borat - November 2006 | The Man Behind the Moustache

Before Borat: Cultural Learnings of America for Make Benefit of Glorious Nation of Khazakhstan, Sacha was relatively unknown in the States beyond a fanbase of rabid HBO devotees and Internet enthusiasts. Upon its release, the film resonated so wildly that following in the grand tradition of Beavis & Butthead, SouthPark, and Austin Powers, the nation became an echo chamber for amateur impressionists. 

2) Entertainment Weekly - Jon Stewart & Stephen Colbert - October 2008 | Mock the Vote

1) Vanity Fair - Tina Fey - January 2009 | What Tina Wants

A searing, memorable cover fit for one of the decade's definitive voices.